Hydrochloric Acid → HCID 69286253, compound

HRID 2373110Notes

Reaction equation

HRID 2373110 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:11]([O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].Cl>[Cu].[Cu]I.CN(C)C=O>[CH2:11]([O:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:20][CH:21]=1)[CH2:12][CH2:13][CH3:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 83742-Chlorobenzoic AcidHCID 11430Potassium CarbonateHCID 312334-Butoxyphenol

Product 1

HCID 69286253HCID 69286253, compoundYield 45.1%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

First, 2-(4-butoxyphenoxy)benzoic acid was prepared. A stirred mixture of 2-chlorobenzoic acid (10.0 g, 64 mmol), 4-butoxyphenol (12.7 g, 77 mmol), potassium carbonate (17.6 g, 128 mmol), copper powder (0.24 g, 3.8 mmol), copper (I) iodide (0.20 g, 1.3 mmol), dithioerithritol (0.20 g, 1.3 mmol), and 75 mL of N,N-dimethylformamide was heated at reflux for 5 h and then cooled to ambient. The reaction mixture was poured onto a mixture of 300 g of ice plus 100 mL of 10% aqueous HCl. The precipitated product was extracted into diethyl ether. The product was purified by extraction into 5% aqueous NaOH, followed by acidification with concentrated HCl. The precipitate was collected, washed with water, and dried in vacuo over CaSO4 to provide 8.27 g (45% of theory) of 2-(4-butoxyphenoxy)benzoic acid as a brown powder.

Workup

  1. customFirst, 2-(4-butoxyphenoxy)benzoic acid was prepared
  2. temperaturewas heated
  3. temperatureat reflux for 5 h
  4. temperaturecooled
  5. extractionThe precipitated product was extracted into diethyl ether
  6. customThe product was purified by extraction into 5% aqueous NaOH
  7. customThe precipitate was collected
  8. washwashed with water
  9. dry with materialdried in vacuo over CaSO4

Sources & evidence

ORD record
ord-bc8a5c16748542c89324f2e12269afa9
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Reaction notes

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